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T144

Sigma-Aldrich

(±)-Thalidomide

≥98%, powder

Sinonimo/i:

(±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

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About This Item

Formula empirica (notazione di Hill):
C13H10N2O4
Numero CAS:
50-35-1
Peso molecolare:
258.23
Numero CE:
200-031-1
Numero MDL:
MFCD00153873
Codice UNSPSC:
12352111
eCl@ss:
39180303
ID PubChem:
24278765
NACRES:
NA.77

ligand

thalidomide

Saggio

≥98%

Forma fisica

powder

Impiego in reazioni chimiche

reagent type: ligand

Colore

white

Solubilità

DMSO: 20 mg/mL, clear

Ideatore

Celgene

Stringa SMILE

O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1

InChI

1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
UEJJHQNACJXSKW-UHFFFAOYSA-N

Informazioni sul gene

human ... CRBN(51185) , CUL4A(8451) , DDB1(1642) , LITAF(9516) , RBX1(9978) , TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)

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Applicazioni

Thalidomide has been used to study its neuropathological effects in mouse models of Alzheimer′s disease (AD). This study reported that long term administration of thalidomide causes beta-secretase inhibition and subsequently alleviates amyloid-like pathology. Furthermore, thalidomide has also been used to evaluate its teratogenic functions. Thalidomide was found to affect endodermal differentiation and neural development in differentiating human embryonic and induced pluripotent stem cells.

Azioni biochim/fisiol

(±)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). It also functions as an inhibitor of angiogenesis, an immunosuppressive agent, a sedative and a teratogen. Furthermore, thalidomide is known to exhibit antitumor functions in refractory multiple myeloma.

Caratteristiche e vantaggi

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Nota sulla preparazione

Thalidomide is soluble in DMSO at a concentration that is more than 20 mg/ml. It is insoluble in water and ethanol.

Applicazioni

N° Catalogo
Descrizione
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Pittogrammi

Skull and crossbonesHealth hazard
GHS06,GHS08

Avvertenze

Danger

Indicazioni di pericolo

H301,H312,H360D

Classi di pericolo

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Repr. 1A

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificati d'analisi (COA)

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Marzia Lazzerini et al.
Inflammatory bowel diseases, 21(8), 1739-1749 (2015-07-18)
In a randomized controlled trial, thalidomide has shown to be effective in refractory Crohn's disease in children. This pilot study aimed at evaluating thalidomide in refractory pediatric ulcerative colitis (UC). Double-blind, placebo-controlled randomized clinical trial on thalidomide 1.5 to 2.5
Tomomi Noguchi et al.
Bioorganic & medicinal chemistry letters, 15(24), 5509-5513 (2005-09-27)
5-Hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione (5HPP-33: 10), which was obtained during our previous structural development studies on thalidomide, was revealed to possess potent anti-angiogenic activity in a human umbilical vein endothelial cell (HUVEC) assay. Thalidomide (1) and its metabolite, 5-hydroxythalidomide (5-HT: 2), which possesses
Yoav Mayshar et al.
Journal of cellular and molecular medicine, 15(6), 1393-1401 (2010-06-22)
Teratogens are substances that may cause defects in normal embryonic development while not necessarily being toxic in adults. Identification of possible teratogenic compounds has been historically beset by the species-specific nature of the teratogen response. To examine teratogenic effects on
S Singhal et al.
The New England journal of medicine, 341(21), 1565-1571 (1999-11-24)
Patients with myeloma who relapse after high-dose chemotherapy have few therapeutic options. Since increased bone marrow vascularity imparts a poor prognosis in myeloma, we evaluated the efficacy of thalidomide, which has antiangiogenic properties, in patients with refractory disease. Eighty-four previously
Marzia Lazzerini et al.
JAMA, 310(20), 2164-2173 (2013-11-28)
Pediatric-onset Crohn disease is more aggressive than adult-onset disease, has high rates of resistance to existing drugs, and can lead to permanent impairments. Few trials have evaluated new drugs for refractory Crohn disease in children. To determine whether thalidomide is
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